Sulfo compounds of quinolin-4-carboxylic acids arylated in the 2 position.



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Tori

a: STATES PATENT FIEICE.

ALsnEorir 'rHiELE, or BERLIN, GERMANH, ASSIGNOR TQ CHEMISGHE FABRIK AUF AGTIEN, (VORIVL E. SCHERING,) or BERLIN, GERMANY.

$31136: CQTMPOUNDS OF QUINOLIN-L-CABBOXYLIC ACIDS ARYLATED IN THE 2 POSITION.

ectare.

To all whom "it may concern Be it known that I, ALBRECHT Ti-IIELE,

- doctor of philosophy. chemist, citizen of the hitherto unknown sulfo compounds of quinolin-a-carboxylic acids arylated in the 2 p0- sit-ion.

The new products have proved to be valuable analget-ics. They have an acidulou's taste and are insoluble in water and organic solvents at ordinary temperature, more or less soluble in hot water, soluble in solutions of alkalis. and alkaline earths and forming salts.

The following examples are methods, of manufacture, the parts being by weight:

(1) 300 parts of 2-phenylquinolin-a-carboxylic acid are heated on an oil bath together with 1600 parts of concentrated sulfuric acid and another 400 parts of sulfuric acid" which contains 7 per cent. of anhydrid for froni-ti to 7 hours ata temperature between 175 and 190 C. After cooling, the fluid is poured into 10000 parts of water and after twenty four hours standing the liquor .is sucked off from the crystalline mass. The sulfo compound when recrys-' tallized. out of per cent. alcohol does not melt at 250 C. but is soluble in hot water, alkali, hot dilute mineral acids and is insoluble in organic solvents.

2 l,in -t carboxylic acid are heated upon an o l bath to 180-l90 C. with the same quantities of sulfuric acid and for the same period as in example {1), the further treatment also taking place as in that example. The comnoiimd obtained crystallizes out of 35 ce "iol. the relations of melting ano Sf y being similar to those previously described.

(3} 250 parts of 2-phenylquinolin--carboxylic acid are subject-ed for about two days to the vapor of sulfuric acid anhydrid at a temperature of from 4L045. C. The mass which. now weighs about another 300 parts added to ice Water and mixed Specification of Letters Patent.

300 parts of 6-methyLQ-phenylquino- Patented Mar. 33, 914.

Application filed October 7, 1913. Serial No. 793,829.

with an excess of carbonateof'lime. The

amountof anacid such as hydrochloric acid. a

Other derivatives can be sulfonated in similarfmariner. I v

The sul'fo compound of Q-phehylquinolinl-carboxylic acid has the structural formula n COOH I claim as my invention:

cuniso u 1. As new products the sulfo compounds I of quinolin-a-carboxylic acids arylated in the 2-position, such compounds'having an acidulous taste, being insoluble in water and organic solvents at ordinary temperature, more or less soluble in hot water, forming salts. and having analgetic properties,

substantially as described.

2. As a new product the sulfo compound of Q-phenylquinolin-4l-carboXylic acid, having the formula v coon being insoluble in water and organic solvents at ordinary temperature, soluble in hot dilute mineral acids as well as, in alkalis and earthalkalis. and having analgetic properties substantially as described.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

DR. ALBRECHT THIELE. Witnesses 'WOLDEMAR HAUPT,

I'IENRY HAsrER. 

